Postcard Southern Tuscany - Cycling Cortona, Montalcino, Siena - Classic Self Guided
Description
Summary
Description
Embark on an unforgettable 8-day journey through the heart of Tuscany, Italy. This multi-day tour offers a unique blend of history, culture, and natural beauty, taking you through ancient Etruscan cities, picturesque hill towns, and stunning landscapes. From the historic city of Cortona to the UNESCO World Heritage landscape of Val d'Orcia, you'll explore some of Italy's most iconic destinations. Savor the region's renowned wines, visit fascinating museums, and soak in the breathtaking views of the Tuscan countryside. Whether you're a history buff, a wine enthusiast, or a nature lover, this tour promises an enriching and immersive experience.
Included
All breakfasts are included
See options for special dinners and meal activities below
vegetarian
Includes
:
7 nights in 3- and 4-star lodgings
All breakfasts
Bike fitting and briefing in English by our professional staff at tour start
Access to smartphone app with tracks and digital roadbook
Luggage transfers
Solo Traveler and Private Group departures
available please inquire.
Lodging Upgrade
: room upgrades are possible in some hotels - please inquire for prices and availability
Private transfers
(please inquire for price and availability)
Florence airport - Cortona
Siena - Florence airport
Extra nights
: If you'd like to add nights before or after the tour, please inquire - we will be happy to provide a quote and add the nights to your tour package.
Extra meals & activities: (please inquire for price and availability)
Cooking classes available in various tour locations! Organized by Le Cesarine, experts in Italian culinary experiences. You will be hosted by a local at their home - your "Cesarina" - in a class that lasts about three hours, during which you will help the Cesarina prepare three courses. In the fourth and final hour, you will enjoy the meal (lunch or dinner) which you prepared during the class. Water and one bottle of house wine for every 3 people are included.
Additional options available:
Wine Tasting in Montalcino
Guided visit of Siena
Bike Rental options:
We offer quality bikes in different styles, all great options for this bike tour. Our bikes are maintained and delivered in optimal working condition.
The prices below are per bike for the duration of the tour, including delivery to starting point in Cortona and collection from ending point in Siena.
Bike rental rates
Aluminum hybrid: €130
Premium Titanium road or hybrid: €170
E-bike (hybrid with straight handlebar): €255
Tandem: €295 (priced per bike, for 2 cyclists)
Tag-along or kid trailer: €80
Map
Attractions
Daily Itinerary
Day 1 – Day 1: Arrival in Cortona
- Cortona - Arrival day
- More
- Etruscan Arch
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Begin your journey in the enchanting hill town of Cortona, overlooking the Chiana River valley. Immerse yourself in the city's rich history, dating back to 600 BC, and explore its medieval character. Visit the Etruscan Museum to delve into the city's ancient past. Your accommodation for the night will be at Hotel S. Luca or a similar establishment.
Day 2 – Day 2: Cortona to Lake Trasimeno
- Cortona
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- Parco Regionale del Lago Trasimeno
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Today, you'll cycle to the shores of Lake Trasimeno, known for its historical significance. Enjoy a boat ride on the lake or simply soak in the serene surroundings. Return to Cortona through the picturesque Tuscan hills. Your accommodation will be at Hotel S. Luca or a similar establishment.
Day 3 – Day 3: Cortona to Montepulciano and Pienza
- Cortona
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- Parterre
- Riserva Naturale Monte Rufeno
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Ride to Montepulciano, famous for its Vino Nobile, and explore the medieval streets of this charming village. After lunch, head to Pienza, one of the first planned Renaissance towns. Discover its architectural beauty and rich history. Your accommodation will be at Relais Il Chiostro di Pienza or a similar establishment.
Day 4 – Day 4: Exploring Val d'Orcia
Day 4: Exploring Val d'Orcia
- Palazzo della Corgna
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Today, you'll cycle through the heart of the Orcia Valley, a UNESCO World Heritage landscape. Experience the changing colors of the rounded hills and explore the medieval village of Monticchiello. Return to Pienza and sample local wines and cheeses. Your accommodation will be at Relais Il Chiostro di Pienza or a similar establishment.
Day 5 – Day 5: Pienza to Montalcino
Day 5: Pienza to Montalcino
- Porta Pispini
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Start your day with a ride through the picturesque Tuscan countryside, making your way to the historic wine town of Montalcino. Explore this fortified hilltop town, famous for its Brunello di Montalcino wine. Your accommodation for the night will be at Hotel dei Capitani or a similar establishment.
Day 6 – Day 6: Montalcino to San Quirico d'Orcia and Bagno Vignoni
Day 6: Montalcino to San Quirico d'Orcia and Bagno Vignoni
- Santuario di Santa Caterina
- Abbey of San Galgano
- Facciatone
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Today's route takes you to the historic Abbey of Sant Antimo, followed by a scenic ride to Castiglione d'Orcia. Visit the charming village of Bagno Vignoni and cycle through San Quirico d'Orcia, an important medieval town. Your accommodation will be at Hotel dei Capitani or a similar establishment.
Day 7 – Day 7: Montalcino to Siena
- Siena
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- Basilica of Saint Margaret of Cortona
- Siena Cathedral
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Pedal to Siena, passing by the historic monastery of Monte Oliveto Maggiore and the eroded chalk hills of the Crete Senesi. Explore Siena, Italy's best-preserved medieval city, and step back in time as you wander through its ancient streets. Your accommodation will be at Hotel Il Chiostro del Carmine or a similar establishment.
Day 8 – Day 8: Departure from Siena
- Siena - Departure day
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Your Tuscan adventure concludes after breakfast. You may choose to extend your stay in Siena, a city worth exploring for another day or two. Alternatively, you can take a train to Florence or Rome for your onward journey.
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